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Synthesis of Furanose Sugar Nucleotides from Mycobacterium tuberculosis and Campylobacter jejuni

  • Author / Creator
    Snitynsky, Ryan Blake
  • Five-membered ring furanose sugars, though absent in mammals, have been found in the cell walls of pathogenic bacteria such as Mycobacterium tuberculosis and Campylobacter jejuni. Because these sugars are only found in microorganisms, it has been proposed that inhibiting the enzymes these bacteria use to process furanose sugars could lead to the development of new targeted treatments against disease. To study these enzymes, access to their natural substrates and analogues is essential. In this work, we explored methods of producing these sugar nucleotides. First, activated donors were used to attempt to make a glycosyltransferase enzyme (GlfT2) work in reverse to produce sugar nucleotides. Subsequently, we attempted to expand the substrate scope of a nucleotidyltransferase (GalPUT). Finally, a wholly synthetic approach was developed to synthesize two nitrogen-containing furanose sugar nucleotides.

  • Subjects / Keywords
  • Graduation date
    2014-06
  • Type of Item
    Thesis
  • Degree
    Master of Science
  • DOI
    https://doi.org/10.7939/R3BV7B405
  • License
    This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.
  • Language
    English
  • Institution
    University of Alberta
  • Degree level
    Master's
  • Department
    • Department of Chemistry
  • Supervisor / co-supervisor and their department(s)
    • Lowary, Todd (Chemistry)
  • Examining committee members and their departments
    • Campbell, Robert (Chemistry)
    • Petersen, Nils (Chemistry)